Olefin metathesis for chemical biology.
Chemical biology relies on effective synthetic chemistry for building molecules to probe and modulate biological function. Olefin metathesis in organic solvents is a valuable addition to this armamentarium, and developments during the previous decade are enabling metathesis in aqueous solvents for the manipulation of biomolecules. Functional group-tolerant ruthenium metathesis catalysts modified with charged moieties or hydrophilic polymers are soluble and active in water, enabling ring-opening metathesis polymerization, cross metathesis, and ring-closing metathesis. Alternatively, conventional hydrophobic ruthenium complexes catalyze a similar array of metathesis reactions in mixtures of water and organic solvents. This strategy has enabled cross metathesis on the surface of a protein. Continuing developments in catalyst design and methodology will popularize the bioorthogonal reactivity of metathesis.
Binder
Joseph B
JB
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706-1322, USA.
Raines
Ronald T
RT
D000475:Alkenes / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry; D011108:Polymers / Q000737:chemistry; D011506:Proteins / Q000737:chemistry; D012995:Solubility
D000475:Alkenes; D006571:Heterocyclic Compounds; D010720:Phosphines; D011108:Polymers; D011506:Proteins; C044646:phosphine